Orlando to Chicago (SFB–MDW) — Airlines, Schedules & Connections

SFB Airport Page →
971 mi airlines charter/private ~1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 13 1-stop flights Verified 6d ago
Charter / private route. No scheduled airline service — operated by charter & private aviation.
Nonstop Charter / private 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

No flights match your filters.

No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.

✦ 1-Stop connections via 10 hubs
CVG Cincinnati / Covington 4h 3m G4 → WN Cincinnati / Covington (CVG) to Chicago flights
TYS Knoxville/Maryville 4h 8m G4 → G4LXJ Knoxville/Maryville (TYS) to Chicago flights
IND Indianapolis 4h 11m G4 → WN Indianapolis (IND) to Chicago flights
SDF Louisville 4h 16m G4 → WN Louisville (SDF) to Chicago flights
PIT Pittsburgh 4h 41m G4 → WN Pittsburgh (PIT) to Chicago flights
GRR Grand Rapids 4h 41m G4 → WN Grand Rapids (GRR) to Chicago flights
BNA Nashville 4h 43m G4 → WN Nashville (BNA) to Chicago flights
ALB Albany 5h 34m G4 → WN Albany (ALB) to Chicago flights
OMA Omaha 5h 44m G4 → LXJWN Omaha (OMA) to Chicago flights
OKC Oklahoma City 9h 30m G4 → WN Oklahoma City (OKC) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Orlando to Chicago
Flown by charter / private operators — no scheduled airline service.
971 mi 2h 27m nonstop -1h behind

SFB–MDW has no scheduled airline service; it is flown by charter / private operators. 1-stop connecting options are also available.

Also explore Browse available seat maps SFB Routes MDW Routes SFB Live Flights MDW Live Flights SFB Delays MDW Delays
All flights from Chicago (MDW) Chicago to Orlando flights
Connections

Connection Landscape

1-stop and 2-stop options for SFB to MDW.
1-STOP
One-Stop Connections
13
Hubs
~4h
Fastest
~11h
Longest
CVG ~4h 3m TYS ~4h 8m IND ~4h 11m SDF ~4h 16m PIT ~4h 41m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
761
Candidates
Two-stop connections loaded in the connections tab above.
Connections computed from published schedules with minimum connection time verification. Use the interactive explorer above the fold to filter by airline, tier, and layover time.
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
SFB → MDW
100%
Generally reliable. Most flights run on time.
Departing
100%
Arriving
100%
Return
MDW → SFB
100%
Generally reliable. Most flights run on time.
Departing
100%
Arriving
100%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. SFB delays → MDW delays →
Alternatives

Other ways to reach Chicago from Orlando

Nearby airports with service to Chicago Midway International Airport.
Metric SFB→MDW MCO→MDW LAL→MDW
Distance from SFB – 24 mi 72 mi
Nonstop airlines – 7 1
Weekly flights ~1 91 –
Flight time 2h 27m 2h 45m 2h 9m
Departure OTP 100% – –
Orlando (MCO) to Chicago flights · Lakeland (LAL) to Chicago flights · St Augustine (UST) to Chicago flights
Airports within 200 miles of SFB with service to Chicago Midway International Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
-1h
Chicago is 1 hour behind Orlando.
SFB: EDT · MDW: CDT

When it's 6:00 PM in Orlando, it's 5:00 PM in Chicago.
Distance & Flight Time
971 mi / 1,562 km
Nonstop flight time is approximately 2h 27m gate to gate.
Facts

SFB–MDW Quick Facts

Key statistics for the Orlando to Chicago route.
Route details
Distance971 mi / 1,562 km
Flight time2h 27m
Time difference-1 hour
Airlines (nonstop)Charter / private
Weekly flights~1 out
1-stop connectionsAvailable
Origin: SFB
Full nameOrlando Sanford International Airport
IATA / ICAOSFB / KSFB
TimezoneAmerica/New_York
Passengers/yr2.8M
Elevation55 ft / 17 m
Destination: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
FAQ

Frequently Asked Questions

Common questions about SFB to MDW flights.
Nonstop flights from Orlando Sanford International Airport to Chicago Midway International Airport take about 2h 27m gate to gate. The route covers 971 miles.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Cincinnati Northern Kentucky, McGhee Tyson and Indianapolis.
On a single ticket, yes. Your bags are checked through to MDW and move between planes without you. On two separate tickets you collect your bags at the connecting airport and recheck them, so build in extra layover time.
Chicago is 1 hour behind Orlando.
Yes, return flights from MDW to SFB are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include MCO, LAL and UST. See the Alternatives section for a full comparison.
Click the 'Search Flights' button to check availability and prices on Google Flights. You can also compare airlines and schedules on this page to find the best option.
See the On-Time Performance section for the latest delay data at both airports. This shows departure and arrival reliability to help you plan.
Route data is updated regularly from official airline schedules. On-time performance data comes from recent airport delay snapshots.

Flights from SFB to MDW

Orlando Sanford International Airport (SFB) and Chicago Midway International Airport (MDW) are connected through multiple connecting hub airports.

SFB to MDW Flight Duration and Schedule

Nonstop flight time from SFB to MDW is about 2 hours 27 minutes gate to gate. The route covers a distance of 971 miles (1,562 km).

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Cincinnati Northern Kentucky, McGhee Tyson and Indianapolis. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Orlando (MCO), Lakeland (LAL) and St Augustine (UST).